2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-9-deoxy-9,10-didehydro-PGH1 cpompounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 647,363,filed Jan. 8, 1976, now issued as U.S. Pat. No. 4,028,419.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,028,419.

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein Y istrans --CH═CH--; wherein M₁ is ##STR2## or ##STR3## wherein R₅ ishydrogen or methyl; WHEREIN L₁ is ##STR4## or a mixture of ##STR5## and##STR6## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, the same ordifferent, with the proviso that one of R₃ and R₄ is methyl only whenthe other is hydrogen or methyl;Wherein g is 1, 2, or 3; and Wherein mis 1 to 5, inclusive.
 2. A compound according to claim 1, wherein m isone or
 2. 3. A compound according to claim 1, wherein m is 4 or
 5. 4. Acompound according to claim 1, wherein m is
 3. 5. A compound accordingto claim 4, wherein g is one.
 6. A compound according to claim 5,wherein at least one of R₃ and R₄ is fluoro.
 7. A compound according toclaim 6, wherein R₃ and R₄ are both fluoro.
 8. A compound according toclaim 7, wherein R₅ is hydrogen. 9.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 8. 10.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 8. 11. A compound according to claim 5,wherein at least one of R₃ and R₄ is methyl.
 12. A compound according toclaim 11, wherein R₃ and R₄ are both methyl.
 13. A compound according toclaim 12, wherein R₅ is hydrogen. 14.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 13. 15.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 13. 16. A compound according to claim 5,wherein R₃ and R₄ are both hydrogen.
 17. A compound according to claim16, wherein R₅ is methyl. 18.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-methyl-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 17. 19.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-epi-15-methyl-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 17. 20. A compound according to claim 16,wherein R₅ is hydrogen. 21.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim
 20. 22.2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-epi-3,7-inter-m-phenylene-4,5,6-trinor-9-deoxy-9,10-didehydro-PGD₁,a compound according to claim 20.